


The Dean Winchester Ride

by Cassie_cas_castiel



Category: Supernatural
Genre: Anxiety Castiel, Awkward Castiel, Destiel - Freeform, Flirt dean, Flirty Dean, Flirty Meg, Fluff, Highschool AU, Jock Dean, Kissing, M/M, Mean Naomi, Nerd Castiel, Playful Dean, Shy Castiel, Teen Castiel, Teen Dean, Teenage destiel, heavy making out, party au
Language: English
Status: Completed
Published: 2018-07-09
Updated: 2018-07-09
Packaged: 2019-06-07 17:07:32
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,674
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15223814
Author URL: https://archiveofourown.org/users/Cassie_cas_castiel/pseuds/Cassie_cas_castiel
Summary: Dean Winchester was a horrible person. Not for being rude or for being a general jerk but because he was so dreamy and awesome and just so nice. He practically blessed this tiny town with his presence.His sun kissed skin. His freckles. Fan fiction green eyes. FAN FICTION LIPS! They were so plump and moisturized that no man or women has or ever will see a chapped lip on Dean Winchester.Bottom line is; Dean Winchester is perfect.Castiel Novak has been riding the Winchester train for what seemed to be a billion and one years.Let’s just say the train is stopping at a station.





	The Dean Winchester Ride

Dean Winchester was like a bad case of baby fever. He came and went, but when he was here, he was here to stay for what felt like years. You knew you were never gonna get him, you just have to ride it out, and hope he never ever looks at you. Once he looks at you, you're whipped, you're done for. Castiel knew this for a fact, he was a soul -not so much survivor- survivor of the Dean Winchester Ride, except he was still whipped. 

You'd think after almost five years of being in a one-sided love with Dean Winchester you'd learn to move on. Perhaps everyone else moved on, but Castiel never did. He was hooked, and made to stay. He was like oatmeal cooked onto the bottom of a pan, he was made to stay. Castiel did try to leave, he really did. He practically pealed himself away from Dean every chance he could, it just didn't work. Whenever Castiel would feel a little bit better, whoop! there's Dean Winchester smiling, and bam! he's back to being whipped. It was actually starting to overwhelm Castiel. 

Castiel growled to himself when he realized just how frustrating getting out of this topic of conversation would be. Michael paced back and forth from wall to wall as he ranted about Gabriel's choice of extracurricular activities, of pranking. "Just this morning I fell into the toilet, Gabriel Novak do you wanna explain that?" To be honest it wasn't as bad as April Fools. This prank didn't consist of, fish, mayonnaise, milk, and other questionable ingredients, just an open toilet seat. 

"Sorry?" Gabriel mumbled, it was quite clear he wasn't if the  smirk on his face wasn't anything to go off of. 

Lucifer -who was undoubtedly late for his shift at a bar called the cage- grumbled, "it just a prank Mikey." He didn't continue when his boyfriend turned around and growled at him. Although Michael was their legal guardian, Lucifer was forced to withstand their almost weekly family discussions. 

"Don't start with me, Lucifer." Lucifer of course immediately backed down from the wrath of a clothing soaked Michael. "I mean come on Gabe, you're a college freshman." 

"Yeah, so?" Gabriel sassed. If it wasn't for the fact he was scared Michael would chew him out, Castiel would have rolled his eyes and marched past the two and out the front door for school. 

"Well aren't you a little too old for pranks?" 

"No one is too old for pranks, Michael." Gabriel finally decidedly stood up from his spot on the couch making his defiance known. "Now, I'd love to stay and chat it out, but I have to take Cassie to school. You know since he's late because of you." 

"Was it because of me, or was it because of your poor timing of a prank?" Michael countered, a small smirk on his face. Castiel heaved a sigh and stood up already making his way toward the front door. 

"Whatever, dickbag," Gabriel called, jumping up the few stairs that separated the family room from the kitchen. "Gabriel and Cassie out!" Gabriel shouted as he shut the front door behind them. 

Castiel jumped into the truck and watched patiently as Gabriel climbed into the driver's side. "Must you always pick a fight with him?" Castiel asked. It wasn't that the three brothers fought often, Castiel knew that Gabriel wouldn't do it if he thought it would jeopardize their brotherly bond. 

"It's just for fun Cassie," Gabriel counseled. Gabriel pulled out of the driveway and clicked his tongue against the roof of his mouth for fun. 

"I mean," Castiel started. "Could you please not start on a school day, more specifically a school morning. I do not wish to be late again." Gabriel rolled his eyes but nodded. 

The drive to the school was short lived. If Castiel was desperate enough he would just have ran, but then again physical activity was his very last option. The school looked to be something out of a cheesy rom com. It's walls were a nice beige color and didn't accommodate the bright red bike racks very well. "Well you're a little late, but I don't think Mrs. Naomi will care too much," Gabriel offered. Castiel knew his brother was wrong. The government teacher was a witch in a pantsuit, she was more Lucifer than Lucifer was. 

"Thanks," Castiel halfheartedly mumbled. Castiel reached down and opened the truck door and got out a little slower than he could have. It wasn't that Castiel didn't like school, he loved school. It was just the fact school required being social, and being social was like a kick in the teeth for Castiel. 

The youngest Novak reluctantly waved his brother off and walked toward the school. His blue and white sweater vest clung to him protectively. Castiel pulled the front door open and scampered into the deserted hallway before he could talk himself out of it. 'Once you are on campus, we are responsible for you,' Mrs. Naomi had said one time. Ever since then Castiel was sure not to leave campus unless given permission, call him a good boy but he was not one to break the rules. 

After checking into the office -and getting a sympathetic look from one of the attendance ladies- Castiel trudged to class waiting for the inevitable shake down every late student got from Mrs. Naomi. Once he made to the door that screamed an eternity of hell he swallowed, he could feel the glare Mrs. Naomi was bound to give him. Despite his already quaking legs and watering eyes Castiel opened the classroom door and immediately regretted it. "Mr. No-vak," She spoke with more venom than any snake could come up with. 

"Yes, ma'am," Castiel responded sheepishly. 

The whole class waited in anticipation, all of them were sympathetic. "To what do we owe the occasion of having Castiel Novak come to MY class over fifteen minutes late, like he owns the world," Mrs. Naomi bit out. So it was so much more worse than Castiel would have liked. Sometimes he wished Mrs. Naomi would be put in her place, but to have that done someone would actually have to be brave enough to do so. 

"My apologies ma'am," Castiel began. He swallowed nervously before continuing, "my brothers wanted to have a family discussion which ran long overdue and I turned up late for school." 

Mrs. Naomi's nose twitched evilly. Her face scrunched momentarily and Castiel thought he almost peed himself -that would have just added to the stack of pancakes he already had on his plate. "And if I were to call your brother he would confirm this?" Mrs. Naomi sneered. Castiel internally flinched at the mention of his brother. It wasn't the fact Michael wouldn't vouch for him, it was what happened after all. It was more of how she said it. Mrs. Naomi had it out for kids who came from broken homes, she sneered at them every chance she got, just because she was a Christian and she didn't believe in divorce. 

"He will," Castiel murmured in embarrassment. If Castiel were to tell Michael any of this, the school would have an angry brother on them in minutes. And Mrs. Naomi would have more of a reason to hate Castiel, which he already didn't enjoy enough as it is. 

Mrs. Naomi growled lowly in her voice, "go sit down Novak." Castiel scrambled to his seat, which was unfortunately behind Dean Winchester, Castiel's not so subtle crush. 

The whole lesson Castiel got sympathetic glances from his peers and the feeling of bile creeping up his throat. The whole class was more behaved than usual seeing as Castiel -the good boy- already got a sneering of a life time. Once the bell rang Castiel was practically flung from his seat, he wasn't too keen on staying for another lecture. 

Castiel walked swiftly to his locker. He needed to exchange his government book for his Algebra book. He internally groaned when he caught sight of black wavy hair and a round face, Meg Masters. 

"So Clarence," Meg Masters began. "Heard you got a mean Naomi on your back this morning'." 

"Yes, you are correct," Castiel mumbled, shuffling his feet. Even though he tutored Meg every other day of the week, the girl's flirty and bored attitude made him uneasy. "Is there anything you wish to acquire from me?" 

"Nothing but love, Clare-ence," Meg stage whispered as she played with the words. Before Castiel could turn her down a dirty laugh exited her throat. "I'm just messin' with you, Clarence." 

"Sometimes I think you are being serious," Castiel admitted, a blush blooming on his cheeks. 

Meg chuckled. "Course not," she mumbled. "Though there is the after game party tonight, I'd really enjoy if you came with me to." 

"I do not wish to participate in drinking," Castiel dismissed, finally unlocking his locker.

"No drinking, Clarence. Just a party." If it wasn't for the fact Meg was so keen on seducing him, he  might have actually been less hesitant on going. The girl wasn't exactly innocent when it came to drugging her dates for sex. 

"Okay," Castiel mumbled. Maybe a party will do some good for his tension. And if Castiel Novak was asked if he was going for Dean Winchester he would have said absolutely not, but the facts were he was. 

Meg smirked nastily before she hummed, "Pick you up at seven, my little tree topper." Castiel wasn't trying to keep his disgust a secret. Being called anything of Meg Master's -besides maybe a friend- was unsettling for him. 

—

The party came way too quickly for Castiel. He was honestly just hoping for it to never come, but unfortunately it did. 

The doorbell rang and Castiel quickly bounded down the stairs to answer it before his brothers could embarrass him. 

Cassie," Michael began. Lucifer was standing behind him giving Castiel a sympathetic look. "Just be careful okay? And call us if you need a ride, even if you've been drinking," Michael sighed. The youngest Novak smiled and nodded and was out the door before Michael could change his mind. 

"Well hiya Clarence," Meg snickered. Castiel refrained from rolling his eyes and climbed into the car. 

Castiel's blue sweater vest and black rimmed glasses practically screamed nerd. If it was for his sex hair and deep blue eyes Castiel would have been worried about his overall appearance. However he had to make a decision, show up in his sweater vest  or show up in his Led Zeppelin shirt and black tight jeans that Gabriel insisted he needed but he didn't want. Castiel went with the safer option seeing as he wasn't too intent on being the parties sex doll. 

"So who is throwing this party?" Castiel asked, curiously. Not that he'd ever care who threw it he just wanted to know if he was expecting a police call or not. 

Meg laughed while she turned her black car a bit too sharply. "Crowley Fergus, baby." 

Crowley was the school's it boy. He specialized in almost every type of substance one could think of, but strangely he never carried anything in the drug category, safe for weed. The school's teachers prided themselves to be diligent and watchful of weed but none of them knew anything, just like the kids wanted them to. Crowley tried to be mean, he did. He practically calls himself the king of hell but everyone knows better, he's actually nice. 

"Oh..." Castiel trailed off. The houses to the right of him looked far more interesting, far more comforting than any conversation he could strike up with Meg. Some houses sported a fountain in their front yard showing off how rich and well off they were, while others simply had flowers and small excuses of trees. 

The car's air was thick and warm, whenever Castiel is in a warm car he gets car sick, or at least that's what he suspects it to be. It doesn't help that the car smelt heavily of lemon perfume to no doubt cover the marijuana stained scent. Castiel wouldn't put it above Meg but he did expect her to at least not do it in her car. 

Just when Castiel glanced behind him into the back seat to see a bright red bong laying casually on a blanket and pillow they pulled up to the house. A spark went through Castiel's stomach when he spotted the undoubtedly 1967 Chevy Impala, Dean Winchester's baby. That meant Dean was at the party for sure, he didn't let anyone drive his baby. 

Castiel gulped nervously. His goal tonight was to get Dean Winchester to talk to him. Of course that wouldn't be easy; the football captain would have cheerleaders and skanks hanging off of him and probably friends galore. Although Castiel didn't go to the game he knew from social media that Dean scored the most points AND led the team to victory. 

"You gettin out or are we going to have sex right here, Clarence?" Meg questioned, a smirk tracing her lips. 

Castiel scrunched his nose up in discomfort and quickly exited the car. Before Castiel even made a step toward the house he quickly wiped his clammy hands off onto his dark blue jeans. 

Meg gasped a laugh but swung her hips onto the yard of the house. They were already a tad late but the guys -and girls- on the front lawn cheered when she sex walked her way up to the door. The blue eyed teenager reluctantly followed her, not daring to swing his hips. Some guys and a few girls catcalled but Castiel shook it off and groaned in embarrassment.  

As soon as the front door was timidly opened and closed behind him Castiel was flung into a flurry of drinking, weed, dancing and public sex. His eyes caught on the sight of a girl giving a guy a blowjob just out in the open. Castiel reminded himself to stay away from the couches and chairs and just to settle for a corner or wall -though he questioned the sanitation of those too. 

The party was reaching its climax, and Castiel was reaching his limit. Dean was nowhere in sight, neither was his baby brother -though Castiel doubted Dean would let him come to this. A few college guys showed and Castiel felt disappointed when one wasn't Gabriel. If Gabriel were here Castiel could just follow him around, and he knew Gabriel would talk and hang out with him. Castiel would catch glimpses of Meg but it was mostly her smoking, drinking, or sticking her tongue down either gender's throat. 

Castiel huffed into his solo cup. His water was getting warm and he really didn't want to go into the kitchen again for another glass, but he didn't trust anyone to get him a new one. Multiple girls have asked if they could, to which Castile politely declined. The room was getting hotter and hotter making Castiel's glasses fog. 

Castiel was just about to call it a night and find his way to the front door when he made eye contact with a girl who was dancing. The girl was pretty, Castiel would admit that. She had brown wavy hair and thick bangs. Her body accommodated her short tight dress very well, she had all the right curves in all the right places. But as the girl -who Castiel thought to be Hannah Hael- grinded on basically anything that would touch her, Castiel felt repulsed. It wasn't that she was a popular, or that she wasn't his type. Believe him he was flattered and considered showing a lying interest but decided not to. As much as Castiel didn't want to admit it, he was gay. It wasn't that he was scared Michael would toss him or anything like that, it was more like he didn't want to get bullied. 

Castiel smiled politely and even waved, but quickly chastised himself for being a dork. Finally ripping his gaze from Hannah, the boy quickly made a decision to go outside and calm his head. He wasn't going to go to the front yard, he didn't want to get catcalled from the stoners again. But he was going to go to the back yard where there was a huge pool and a porch with soft looking chairs. 

It was a bit of a surprise to Castiel when there was not anyone in sight, maybe Crowley set rules before each party. Castiel knew it was too cold for a swim but indulged himself to at least take off his shoes and socks and dip his feet. The water was lukewarm which made Castiel assume it was heated. 

The pool had dim lights shining at the bottom, it seemed to be something out of a movie. Castiel almost cringed when he thought about how cheesy he was being, he wasn't a girl and he wasn't in a movie. If Mrs. Naomi were to be able to tap into his mind he was sure she would laugh cruelly at him. 

"Shocker to see you here." Castiel looked up from the pool and met sight with Dean Winchester. He was almost discouraged but instead blushed and looked down to his lap.

"I'm kinda surprised to be here," Castiel agreed, "it's not really my scene."

"What? You don't like loud druggie parties with a hint of alcohol to hide the marijuana on your breath?" Dean mockingly laughed. 

Castiel laughed as well. "Call me crazy but I don't." 

"Oh crazy? No-o." Dean sat himself down next to Castiel putting his already bare feet in the water. "Let's just call you... spontaneous?" 

Castiel giggles while lifting his feet in and out of the water. Too embarrassed to look Dean in the eye, he simply watched the water slip down his legs and back into the water. 

"Why are you here Cas? Gabriel ain't here," Dean asked, looking at the slimmer boy. 

"Well. . ." Castiel began. "I wanted to try something new." 

"So you skip the three friend get togethers and go straight to the grind fest? Good choice," Dean teased, licking his lips and laughing. 

"Though I did just get eye raped by Hannah Hael, I've quite enjoyed my skipping." Castiel knew he was lying. He didn't want to be at the party. It was partially because it was practically a glory hole with just some added drugs and dancing as well as music. 

"Shit dude," Dean laughed, "you got eye-fucked by Hannah Hael? Did you like it?" 

"Absolutely not. You know considering she's not the right gender AND she was grinding on anything that would touch her. I'm sure she even grinded on a table because she touched it." 

"Woah, woah, woah." Castiel knew he messed up. Dean Winchester knew he was gay, that was a big enough screw up then anyone could ever fix. "You're gay?" 

"Umm," Castiel stuttered. The big blue eyed boy shyly glanced to Dean only to see a don't-lie-to-me face. Castiel sighed heavily, "yes?"

“I’ve always wanted to know a gay guy!” Dean exclaimed. 

“Oh?” It wasn’t exactly the response Castiel was looking for. 

“Hey can I try something?!” Dean bursted out. He was almost like an excited puppy. 

Castiel hummed thinking about it. It wasn’t like Castiel was assuming Dean would do anything bad but he also couldn’t be absolutely trusted. “I guess, why not.” 

“Awesome!” Dean reached out and cradled Castiel’s cheeks softly. Castiel stuttered and practically blew up into a red mess. “Just relax,” Dean soothed, as he got closer and closer. Castiel watched anxiously as Dean slowly slid his eyes shut. Realizing it was probably weird to kiss (or at least that’s what he think Dean is gonna do) with his eyes open, Castiel snaps them shut and waits. 

It was soft. His lips were so soft and if Castiel knew any better he’d say they were heaven’s lips. Dean kissed so gently and yet so urgently, it was getting caught in a snowstorm, so gentle, so dominant. Dean pressed forward trying to get any kind of response out of his kissing partner. Castiel whimpered before hesitatingly pressing back. That’s when Dean started working his lips against Castiel’s. The poor blue eyed boy didn’t know what to do but sit there and try not to cough or peek at Dean. 

When Dean licked up into his mouth, Castiel quickly opened his mouth. It was so erotic. . . so dirty. Having another man’s tongue in your mouth was like giving god and his angels the middle finger. Castiel couldn’t help but love it. 

Dean slowly pulled back. His stomach flipped excitedly when he caught sight of the spit line that connected his and Castiel’s lips together. Blue eyes slowly opened to catch sight of Dean’s fan fiction green eyes coming closer and closer to him. Assuming the boy wanted more kisses Castiel snapped his eyes shut. A sweet peck grazed his lips before Castiel felt a weight balanced softly against his forehead. A light touch on his nose. 

Castiel opened one eye and almost gasped when bright green along with sun kissed freckled skin was all he saw. Dean was hovering above his lips, almost expectantly but also not. The boy shivered at the others dominating confidence. Finding courage Castiel quickly kissed up on Dean’s swollen plump lips before almost dying out of embarrassment. Due to so much wiggling and nerves. Castiel only managed to kiss Dean’s lips once before kissing the side of his mouth multiple times. 

Dean chuckled at the other boy’s adorable clumsiness. “You’ve never done this before- have you?” Dean asked, his voice a soft whisper as if the words were only meant for them. 

Castiel nodded. “I haven’t,” he stammered. 

Dean nodded and smiled wide. “Good,” he whispered before reattaching their lips. 

Dean slowly guided Castiel to kiss with more confidence. By the time the party actually ended Castiel’s lips were swollen, Castiel was in a daze, and his new boyfriend wasn’t much better.

**Author's Note:**

> I do not own Supernatural or any of its characters. No copy right infringement intended.


End file.
